An efficient synthesis of benzylidene-2-alkoxy-4-aryl-2,3-cycloalkenopyridine-3-carbonitrile derivatives

References

• Debnath, B.; Singh, W. S.; Das, M.; Goswami, S.; Singh, M. K.; Maiti, D.; Manna, K. Role of Plant Alkaloids on Human Health: A Review of Biological Activities. Mater. Today Chem. 2018, 9, 56–72. DOI: 10.1016/j.mtchem.2018.05.001.
   Web of Science ®Google Scholar
• Akhtar, J.; Khan, A. A.; Ali, Z.; Haider, R.; Yar, M. S. Structure-Activity Relationship (SAR) Study and Design Strategies of Nitrogen-Containing Heterocyclic Moieties for Their Anticancer Activities. Eur. J. Med. Chem. 2017, 125, 143–189. DOI: 10.1016/j.ejmech.2016.09.023.
   PubMed Web of Science ®Google Scholar
• McAteer, C. H.; Balasubramanian, M.; Murugan, R. Pyridines and Their Benzo Derivatives: Applications. CHEC-III. 2008, 7, 309–336. DOI: 10.1016/B978-008044992-0.00606-4.
   Google Scholar
• Manna, F.; Chimenti, F.; Bolasco, A.; Bizzarri, B.; Filippelli, W.; Filippelli, A.; Gagliardi, L. Anti-Inflammatory, Analgesic and Antipyretic 4,6-Disubstituted-3-Cyano-2-Aminopyridines. Eur. J. Med. Chem. 1999, 34, 245–254. DOI: 10.1016/S0223-5234(99)80057-9.
   Web of Science ®Google Scholar
• Quintela, J. M.; Peinador, C.; Botana, L.; Estevez, M.; Riguera, R. Synthesis and Antihistaminic Activity of 2-Guanadino-3-Cyanopyridines and Pyrido[2,3-d]-Pyrimidines. Bioorg. Med. Chem. 1997, 5, 1543–1553. DOI: 10.1016/S0968-0896(97)00108-9.
   PubMed Web of Science ®Google Scholar
• McClure, D. E.; Baldwin, J. J.; Randall, W. C.; Lyon, T. F.; Mender, K.; Lundell, G. F.; Raab, A. W.; Gross, D.; Risley, E. A.; Sweet, C. S.; et al. Antihypertensive.beta.-Adrenergic Blocking Agents: N-Aralkyl Analogs of 2-[3-(Tert-Butylamino)-2-Hydroxypropoxy]-3-Cyanopyridine. J. Med. Chem. 1983, 26, 649–657. DOI: 10.1021/jm00359a006.
   PubMed Web of Science ®Google Scholar
• Khidre, R. E.; Abu-Hashem, A. A.; El-Shazly, M. Synthesis and anti-Microbial Activity of Some 1-Substituted Amino-4,6-Dimethyl-2-Oxo-Pyridine-3-Carbonitrile Derivatives. Eur. J. Med. Chem. 2011, 46, 5057–5064. DOI: 10.1016/j.ejmech.2011.08.018.
   PubMed Web of Science ®Google Scholar
• Mohamed, L. W.; Shaaban, M. A.; Zaher, A. F.; Alhamaky, S. M.; Elsahar, A. M. Synthesis of New Pyrazoles and Pyrozolo[3,4-b]Pyridines as anti-Inflammatory Agents by Inhibition of COX-2 Enzyme. Bioorg. Chem. 2019, 83, 47–54. DOI: 10.1016/j.bioorg.2018.10.014.
   PubMed Web of Science ®Google Scholar
• El-Sayed, N. S.; Shirazi, A. N.; El-Meligy, M. G.; El-Ziaty, A. K.; Rowley, D.; Sun, J.; Nagib, Z. A.; Parang, K. Synthesis of 4-Aryl-6-Indolylpyridine-3-Carbonitriles and Evaluation of Their Antiproliferative Activity. Tetrahedron Lett. 2014, 55, 1154–1158. DOI: 10.1016/j.tetlet.2013.12.081.
   PubMed Web of Science ®Google Scholar
• Ulloora, S.; Shabaraya, R.; Aamir, S.; Adhikari, A. V. New Imidazo[1,2-a]Pyridines Carrying Active Pharmacophores: Synthesis and Anticonvulsant Studies. Bioorg. Med. Chem. Lett. 2013, 23, 1502–1506. DOI: 10.1016/j.bmcl.2012.12.035.
   PubMed Web of Science ®Google Scholar
• Kim, K.-R.; Rhee, S.-D.; Kim, H. Y.; Jung, W. H.; Yang, S.-D.; Kim, S. S.; Ahn, J. H.; Cheon, H. G. KR-62436, 6-{2-[2-(5-Cyano-4,5-Dihydropyrazol-1-yl)-2-Oxoethylamino]Ethylamino}Nicotinonitrile, is a Novel Dipeptidyl peptidase-IV (DPP-IV) Inhibitor with anti-Hyperglycemic Activity. Eur. J. Pharmacol. 2005, 518, 63–70. DOI: 10.1016/j.ejphar.2005.05.030.
   PubMed Web of Science ®Google Scholar
• Ibrahim, T. S.; El-Sayed, H. A.; Khayat, M. T.; Al-Mahmoudy, A. M. M.; Moustafa, A. H.; El-Deen, A. K. S.; Rostom, S. A. F.; Panda, S. S. Sythesis of Nucleosides and Non-Nucleosides Based 4,6-Disubstituted-2-Oxo-Dihtydropyridine-3-Carbonitriles as Antiviral Agents. Med. Chem. 2018, 14, 791–808. DOI: 10.2174/1573406414666180522123524.
   PubMed Web of Science ®Google Scholar
• Song, Y.-L.; Tian, C.-P.; Yan, W.; Jiang, L.; Shen, L.-Q. Design, Synthesis and Antitumor Activity of Steroidal Pyridine Derivatives Based on Molecular Docking. Steroids 2019, 143, 53–61. DOI: 10.1016/j.steroids.2018.12.007.
   PubMed Web of Science ®Google Scholar
• Abdelaziz, M. E.; El-Miligy, M. M. M.; Fahmy, S. M.; Mahran, M. A.; Hazzaa, A. A. Design, Synthesis and Docking Study of Pyridine and Thieno[2,3-b]Pyridine Derivatives as Anticancer PIM-1 Kinase Inhibitors. Bioorg. Chem. 2018, 80, 674–692. DOI: 10.1016/j.bioorg.2018.07.024.
   PubMed Web of Science ®Google Scholar
• Abouzid, K. M.; Al-Ansary, G. H.; El-Naggar, A. M. Eco-Friendly Synthesis of Novel Cyanopyridine Derivatives and Their Anticancer and PIM-1 Kinase Inhibitory Activities. Eur. J. Med. Chem. 2017, 134, 357–365. DOI: 10.1016/j.ejmech.2017.04.024.
   PubMed Web of Science ®Google Scholar
• Davari, A. S.; Abnous, K.; Mehri, S.; Ghandadi, M.; Hadizadeh, F. Synthesis and Biological Evaluation of Novel Pyridine Derivatives as Potential Anticancer Agents and Phosphodiesterase-3 Inhibitors. Bioorg. Chem. 2014, 75, 83–89. DOI: 10.1016/j.bioorg.2014.09.003.
   Web of Science ®Google Scholar
• Shamroukh, A. H.; El-Shahat, M.; Drabowicz, J.; Ali, M. M.; Rashad, A. E.; Ali, H. S. Anticancer Evaluation of Some Newly Synthesized N-Nicotinonitrile Derivative. Eur. J. Med. Chem. 2013, 69, 521–526. DOI: 10.1016/j.ejmech.2013.09.005.
   PubMed Web of Science ®Google Scholar
• Rostom, S. A. F.; Bekhit, A. A. Microwave-Assisted Synthesis of Certain Pyrrolylpyridines, Some Derived Ring Systems and Their Evaluation as Anticancer and Antioxidant Agents. Eur. J. Med. Chem. 2015, 92, 712–722. DOI: 10.1016/j.ejmech.2015.01.023.
   PubMed Web of Science ®Google Scholar
• Ragab, H. M.; Teleb, M.; Haidar, H. R.; Gouda, N. Chlorinated Tacrine Analogs: Design, Synthesis and Biological Evaluation of Their anti-Cholinesterase Activity as Potential Treatment for Alzheimer’s Disease. Bioorg. Chem. 2019, 86, 557–568. DOI: 10.1016/j.bioorg.2019.02.033.
   PubMed Web of Science ®Google Scholar
• Dodiya, D. K.; Ram, H. K.; Trivedi, A. R.; Shah, V. H. An Efficient, Microwave-Assisted, One-Pot Synthesis of Novel 5,6,7,8-Tetrahydroquinoline-3-Carbonitriles. J. Serb. Chem. Soc. 2011, 76, 823–830. DOI: 10.2298/JSC100702071D.
   Web of Science ®Google Scholar
• Calhoun, W.; Carlson, R. P.; Crossley, R.; Datko, L. J.; Dietrich, S.; Heatherington, K.; Marshall, L. A.; Meade, P. J.; Opalko, A.; Shepherd, R. G. Synthesis and Antiinflammatory Activity of Certain 5,6,7,8-Tetrahydroquinolineas and Related Compounds. J. Med. Chem. 1995, 38, 1473–1481. DOI: 10.1021/jm00009a008.
   PubMed Web of Science ®Google Scholar
• Gouda, M. A.; Berghot, M. A.; Abd El Ghani, G. E.; Khalil, A. E.-G. M. Chemistry of 2-Amino-3-Cyanopyridines. Synth. Commun. 2014, 44, 297–330. DOI: 10.1080/00397911.2013.823549.
   Web of Science ®Google Scholar
• Mohan, R. B.; Reddy, N. C. G.; Kumar, S. D. Synthesis of Alkynyl/Alkenyl-Substituted Pyridine Derivatives via Heterocyclization and Pd-Mediated Sonogashira/Heck Coupling Process in One-Pot: A New MCR Strategy. RSC Adv. 2014, 4, 17196–17205. DOI: 10.1039/C4RA01053A.
   Web of Science ®Google Scholar
• Amer, A. A.; Abdelhamid, A. A. Microwave-Assisted, One-Pot Multicomponent Synthesis of Some New Cyanopyridines. J. Heterocyc. Chem. 2017, 54, 3126–3132. DOI: 10.1002/jhet.2926.
   Web of Science ®Google Scholar
• Riadi, Y.; Mamouni, R.; Routier, S.; Guillaumet, G.; Lazar, S. Ecofriendly Synthesis of 3-Cyanopyridine Derivatives by Multi-Component Reaction Catalyzed by Animal Bone Meal. Environ. Chem. Lett. 2014, 12, 523–527. DOI: 10.1007/s10311-014-0478-y.
   Web of Science ®Google Scholar
• Bahrami, K.; Khodaei, M. M.; Naali, F.; Yousefi, B. H. Synthesis of Polysubstituted Pyridines via Reactions of Chalcones and Malononitrile in Alcohols Using Amberlite IRA-400 (OH-). Tetrahedron Lett. 2013, 54, 5293–5298. DOI: 10.1016/j.tetlet.2013.07.080.
   Web of Science ®Google Scholar
• Xin, X.; Wang, Y.; Kumar, S.; Liu, X.; Lin, Y.; Dong, D. Efficient One-Pot Synthesis of Substituted Pyridines through Multicomponent Reaction. Org. Biomol. Chem. 2010, 8, 3078–3082. DOI: 10.1039/c001117g.
   PubMed Web of Science ®Google Scholar
• Al-Arab, M. M. A Facile Synthesis of 6-Alkoxy-2,4-Diaryl-5-Cyanopyridine. J. Heterocycl. Chem. 1989, 26, 1665–1673. DOI: 10.1002/jhet.5570260629.
   Web of Science ®Google Scholar
• Heravi, M. M.; Zadsirjan, V.; Dehghani, M.; Ahmadi, T. Towards Click Chemistry: Multicomponent Reactions via Combinations of Name Reactions. Tetrahedron 2018, 74, 3391–3457. DOI: 10.1016/j.tet.2018.04.076.
   Web of Science ®Google Scholar
• Radwan, M. A. A.; Abbas, E. M. H. Synthesis of Some Pyridine, Thiopyrimidine, and Isoxazoline Derivatives Based on the Pyrrole Moiety. Monatsh. Chem. 2009, 140, 229–233. DOI: 10.1007/s00706-008-0061-y.
   Web of Science ®Google Scholar